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(1) Background: Obesity, a poor diet, and inactivity are major health issues among Saudi youth. However, satisfaction with unhealthy lifestyles could impede change. This study assessed lifestyle factors and related satisfaction among Saudi university students. (2) Methods: In this cross-sectional study, 1957 students at Jazan University completed surveys on demographics, physical activity, dietary habits, and 10-point satisfaction scales for weight, activity, and diet. Chi-squared tests and logistic regression were used to analyze the associations between behaviors and satisfaction. (3) Results: Overweight/obesity prevalence was 25.45%, and only 26.67% of the subjects met activity guidelines. Many of them exhibited poor dietary habits. Despite unhealthy behaviors, some expressed high satisfaction, especially regarding their diets. Subjects with a normal BMI had the highest weight satisfaction. Activity satisfaction increased with higher activity levels. Dietary satisfaction was minimally impacted by healthfulness. Males and higher incomes were correlated with greater satisfaction. (4) Conclusions: A concerning paradox exists between unhealthy lifestyles and satisfaction among Saudi university students, particularly regarding their diets. Multicomponent interventions informed by behavior change theories and employing motivational techniques are urgently needed to address this disconnect and facilitate positive behavior change.